Diisopropylethylamine → HCID 67101915, compound

HRID 2079678Notes

Reaction equation

HRID 2079678 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[C:8]2[C:3]=1[CH:4]=[N:5][C:6]([NH:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][C:21]=1[O:29][CH3:30])=[N:7]2.N[CH:32]1[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]1.C[N:40](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)=[C:8]2[C:3]=1[CH:4]=[N:5][C:6]([NH:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:40][CH:36]3[CH2:37][CH2:32][CH2:33][CH2:34][N:35]3[CH3:38])=[O:25])=[CH:22][C:21]=1[O:29][CH3:30])=[N:7]2

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59199297HCID 59199297, compound

Product 1

HCID 67101915HCID 67101915, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-(5-bromo-8-(piperidine-4-yloxy)quinazolin-2-ylamino)-3-methoxybenzoic acid (1 eq), 4-amino-N-methylpiperidine (2 eq), HATU (1.5 eq) and DIEA (3 eq) in NMP was stirred at room temperature for 4 h. The reaction mixture was concentrated and purified by semi-prep HPLC to provide pure product in 45% yield.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by semi-prep HPLC
  3. customto provide pure product in 45% yield

Sources & evidence

ORD record
ord-9128756dcf6b45ba8b6a736867e83a2b
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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